I've used Westone IEMs for maybe 10 years now. Usually with foam tips, lately Comply. You can tell when the seal goes or the foam starts to loosen as well. I did once get some custom tips but they make them from solid vinyl which while usually comfortable, means that any change to your ear shape, i.e. caused by regular use of earplugs makes it really difficult to get them to seal. So I went back to Comply tips

At home I use some 20 year old KEF speakers, never for critical listening (what is that anyway?) as the road I live on is too noisy for that usually.